| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SUN 9/15 | 2:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 14-17 | | Tiger Hollow Stadium | |
| FRI 9/20 | 7:00 p.m. | Varsity | League | Normal | Home | LymanHall | Win | 47-7 | | Cheshire High Main Game field | |
| FRI 9/27 | 7:00 p.m. | Varsity | League | Normal | Home | WestHaven | Loss | 20-48 | | Cheshire High Main Game field | |
| FRI 10/4 | 6:00 p.m. | Varsity | League | Normal | Away | Sheehan | Win | 28-27 (OT) | | Sheehan HS Riccitelli Field | |
| FRI 10/11 | 7:00 p.m. | Varsity | League | Normal | Home | DanielHand | Loss | 24-35 | | Cheshire High Main Game field | |
| FRI 10/18 | 7:00 p.m. | Varsity | League | Normal | Home | Hamden | Win | 13-6 | | Cheshire High Main Game field | |
| FRI 10/25 | 6:00 p.m. | Varsity | League | Normal | Away | FairfieldCollegePreparatory | Loss | 0-26 | | Alumni Field, Fairfield University | |
| FRI 11/1 | 7:00 p.m. | Varsity | League | Normal | Away | NotreDame | Loss | 0-28 | | Veteran's Stadium | |
| FRI 11/8 | 7:00 p.m. | Varsity | League | Normal | Home | AmityReg | Win | 34-13 | | Cheshire High Main Game field | |
| SAT 11/16 | 12:01 p.m. | Varsity | League | Normal | Away | WilburCross | Loss | 13-40 | | Wilbur Cross Athletic Complex | |
| THU 11/28 | 10:00 a.m. | Varsity | League | Normal | Home | Southington | Loss | 6-38 | | Cheshire High Main Game field | |